Well, other than passing through on the way to CA a few times as a very young person, all my experience in that little corner of heaven was on the way from Dallas to Terlingua and on the way back to Dallas from Terlingua, three times.
It was a ritual to go in one way, through Marathon and come out a different way, through Alpine. We'd meet the Houston and San Angelo contingent in Marathon and then there is a special totem to the chili gods in a trailer park on the way into town - I believe it's at Study Butte, but seems like it's earlier than that - that we had to stop and kiss and give offerings to.
After that, coming back out was just a matter of seeing different breath-taking scenery on the way back to Monahans and points east. No one would ever take me to Marfa or go with me if I was driving, although I always begged.
I haven't been there too much myself, but my dad fell in love with the area after going to a star party in the Ft Davis area and moved out there first chance he got.
I kid him that he moved out there cause it's over a hundred miles to the nearest Walmart, a place he used to visit much too often back in Houston and in Irving.